Into The Wild: A Year of Working Independently Teaches Lessons In Humility, Ego and Direction

The past year was one of enormous growth, as I started the journey of figuring out what was next, who I am and what I want to do. This comes on the heels of a 2013 that saw me leave the company I had determinedly worked at for almost a decade. I say determinedly because I stayed too long and gave up too much in the process. Don’t get me wrong. I got a lot out of it. But after a period of reflection, I began to awaken to what was lost in the bargain.

You see, when things go bad, I have a tendency to bury my head, grit my teeth and just get through it. I grew up in challenging situations and had to deal with whatever got thrown my way, so that’s just my general mode of being. When the end came I had invested so much of my time and effort in the company—and tied myself so closely to it—that I couldn’t discern where the company ended and I began.

The details of what happened were mildly shocking and yet exceedingly mundane. It’s your typical new-guy-cuts-you-out-while-presenting-your-work-as-his-and-positions-himself-as-the-future-while-a-new-investor-demands-big-changes type of thing. My company had a layoff and I was out, along with a whole management layer.

I knew it was coming months in advance. I was ready for it. Steeled even. But afterwards my emotions caught me by surprise. For about three months after the layoff I was confused. And then sad. And then exceptionally angry. And then even more exceptionally angry.

It started three years before the end. In typical fashion, I had thrown myself into a new job and was determined to make it work, regardless of the writing on the wall: the company where I was working at was not the company that I had joined.

You see, my company had to change its strategy because of the massive growth of mobile. It led to many more people using our products, which was awesome. It also became important that the company shored up its knowledge and connections in the cellular carrier business, as those partnerships would turn on an endless spigot of new customers.

Meanwhile since the day I started, the company had lost a long line of what I called the ‘true believers.’ Those who were inspired to change the music industry by creating an addictive experience for music fans and new revenue for musicians. A major turning point occurred when the company lost one of the longest-tenured and most influential of the true believers; perhaps the person who served as our musical soul.

Later, over lunch, he mentioned that he wished he left earlier. Like when it was obvious that things had changed. I made a mental note. I was absolutely sure my time would come, as it had for many of my former colleagues, and I wanted to act before that day. Instead, I took up the flag for the company. I doubled down in loyalty and effort, even as people left and were replaced by new employees with cellular carrier experience instead.

The fact is when the people changed, the place changed. The new direction made sense, but the company had a different feel. Instead of recognizing this, I tried to keep a culture alive that didn’t exist anymore. I even hired a career coach to help me through it. After sitting down the first time and describing my situation, she asked why I wanted to be at my company. Because I have to make it work, I said. But why, she asked.

Her point was that no matter how hard you try a company’s culture is the most important factor in determining your professional success. It might fit you. It might not. If it doesn’t, there is no reason to continue working there.

My coach pointed out that I was trying to fit into a company that seemed different from my values. I listened closely, knew what she said was true, and then quickly ignored the advice. It worked for a while. I got promoted and moved up. But in that exchange, I started to lose something important. My instincts.

I started to question if I really fit. And instead of hearing the words of my coach, I adapted to the new direction. Instead of just being me, it felt like I was playing the part of someone I wasn’t. Granted I learned much from the new regime: you can always learn if you pay attention. But if I’m being honest with myself, I was relying on the trappings of the new direction rather than just being myself and letting that be enough.

So after a couple months of processing and 2014 dawned, I was ready to reclaim me. My release back into the career wild has led me to rediscover my love for writing and analysis, choose who I want to work with and tackle problems that can potentially make a difference in our industry.

And it’s paying off. I’ve attracted a small but influential audience of readers. I worked with a handful of innovative clients. And have found time to consider and communicate new ways to approach the business.

It’s far from easy. There are tough days as assignments and income can be sporadic. Sometimes I lose the thread of what I’m doing. Some days my ego gets the best of me and I wonder if think I’m so good then why am I on the sidelines. Other days, I question my talents and abilities. And I have more work to do. Plus there’s the downside of being highly adaptable: I’ve done many jobs because I can do them instead doing what I really want to do. But instead of losing years trying to fit in, I’m now forced to examine what I stand for and who I am.

I trust myself more. I’m even getting better at introducing myself as Jon instead of somebody who does something at a company. I’ve stricken the ‘we’ when talking or thinking about my former employer and its challenges.

Steve Jobs famously said that getting fired from Apple freed him to have “the lightness of being a beginner.” Today let’s toast that lightness of seeing things from the beginning.

6 thoughts on “Into The Wild: A Year of Working Independently Teaches Lessons In Humility, Ego and Direction”

So is that what Milan Kundera was getting at? I never understood what that meant before , but I think I do now, though apparently he felt his lightness of being was a bit unbearable. Thanks for the story Jon. Godspeed in 2015!